Highly Enantioselective Aza Morita-Baylis-Hillman Reaction Catalyzed by Bifunctional beta -Isocupreidine Derivatives

The aza-MBH reaction of imines, e.g., I, and beta -naphthyl acrylate in the presence of C-6' modified beta -isocupreidine deriv. (0.1 equiv) and beta -naphthol (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts, e.g., II, in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliph. imines to be employed for the first time as electrophilic partners of the aza-MBH reaction. The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the obsd. high enantioselectivity. [on SciFinder (R)]


Published in:
Journal of the American Chemical Society, 130, 38, 12596-12597
Year:
2008
Keywords:
Imines Role: RCT (Reactant) ; RACT (Reactant or reagent) (aldimines; stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); Amino acids Role: SPN (Synthetic preparation) ; PREP (Preparation) (esters ; alpha -methylene; stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); Baylis-Hillman reaction (stereoselective aza; stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); Stereoselective synthesis (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); Alkaloids Role: CAT (Catalyst use) ; SPN (Synthetic preparation) ; PREP (Preparation) ; USES (Uses) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); Addition reaction catalysts (stereoselective ; Baylis-Hillman; stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate) ; imine acrylate isocupreidine enantioselective aza Morita Baylis Hillman; amino methylene carboxylic ester stereoselective prepn; enantioselective aza Morita Baylis Hillman catalyst isocupreidine
Note:
CAN 149:355419
23-17
Aliphatic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0002-7863
written in English.
253430-48-7; 890043-55-7 Role: CAT (Catalyst use), USES (Uses) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 1056903-96-8P Role: CAT (Catalyst use), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), USES (Uses), RACT (Reactant or reagent) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 1056903-97-9P; 1056903-98-0P; 1056903-99-1P; 1056904-00-7P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 23165-29-9; 35150-06-2; 35150-09-5; 52684-34-1 (beta -Naphthyl acrylate); 52960-60-8; 52960-63-1; 129095-62-1; 612063-38-4; 656835-59-5; 656835-60-8; 890043-99-9; 1056904-01-8; 1056904-02-9; 1056904-03-0; 1056904-04-1; 1056904-05-2; 1056904-06-3; 1056904-07-4; 1056904-08-5; 1056904-09-6; 1056904-10-9; 1056904-11-0 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate); 1056904-12-1P; 1056904-13-2P; 1056904-14-3P; 1056904-15-4P; 1056904-16-5P; 1056904-17-6P; 1056904-18-7P; 1056904-19-8P; 1056904-20-1P; 1056904-21-2P; 1056904-22-3P; 1056904-23-4P; 1056904-24-5P; 1056904-25-6P; 1056904-26-7P; 1056904-27-8P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of beta -amino-alpha -methylene carboxylic esters via beta -isocupreidine derivs.-catalyzed enantioselective aza Morita-Baylis-Hillman reaction of imines with naphthyl acrylate)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)